


Good Boy / Bad Boy

by JackTrades



Series: I Like To Watch [4]
Category: Supernatural
Genre: Bondage, Cunnilingus, Dirty Talk, Dominatrix, F/M, Facials, M/M, Masturbation, Praise Kink, Rough Sex, Sex Toys, Spanking, Voyeurism, Wincest - Freeform
Language: English
Status: Completed
Published: 2015-08-18
Updated: 2015-08-18
Packaged: 2018-04-15 07:54:24
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,165
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4598826
Author URL: https://archiveofourown.org/users/JackTrades/pseuds/JackTrades
Summary: <blockquote class="userstuff">
              <p>Dean find out that Sam secretly wants his partners to be rougher with him during sex, and suggests that he be Sam's backup when Sam tries it out.</p>
<p>Can be read as a standalone or as part of the series.</p>
            </blockquote>





	Good Boy / Bad Boy

**Author's Note:**

> This one is far more plot than my other works. Constructive feedback is always appreciated.
> 
> If you are reading this as a standalone, here's the only information you need to know about the previous installments: Dean watched Sam have sex with a random girl, then Sam did the same with Dean, finally they broke down and had a threesome where they both took it too far.

After the threesome incident, they talked about it.  And talked about it.  Aaaand talked about it.   

Dean apologized profusely for taking it too far with the dirty talk.  Sam apologized for provoking it in the first place.  It hadn't occurred to either of them that in the heat of the moment caution and filters would go out the window.  Sam nursed a busted, bruised lip for a week.  He would wince occasionally when he accidentally bit it himself as it was healing, but something else about it seemed off to Dean.  Not off off, just Sam off.   

Dean finally got his opportunity to say something in the car when he hit an unexpected pothole while Sam was mid-sip on his bottle of water.  The sudden jarring of the car had Dean cursing and smacked the bottle into Sam's still-tender mouth.  Sam let out a moan as he grabbed handful of napkins to clean up the water he spilled on himself. 

"Son of a bitch!" Dean checked on Sam as he was wiping his shirt, "You okay over there? Sounded like one of your sexy moans instead of a pain one - you couldn't have been that thirsty?" Sam stiffened and paused for barely a second.  It was just enough of a tell.  Dean knew he hit a nerve and he was going for it. "What? You like reinjuring yourself? Do you get off on the pain or something? Kinky, Sam." He wagged his eyebrows as he cracked a shit-eating grin at Sam. 

"Shut up, jerk," still cleaning his shirt. 

"I didn't put a freaking pothole there - and don't accuse me of doing it on purpose! I'm pulling over at the first gas station we find to check her undercarriage!" 

They drove for almost an hour before Dean's mental landmine got the better of Sam. Sometimes those worked, even if Dean didn’t intentionally put one there.  "So what if I do get off on the pain? What's it to you?" 

Dean perked up, "Hey, I was just busting your balls but if you enjoy it, whatever. Different strokes for different folk.  Glad to be still getting you off even after our little tango with what's her name." Then he turned and winked at Sam.  If the cocky bastard wasn't driving, Sam would have punched him. 

"I hate you," Sam refused to further discuss this.  He turned and looked out his window while Dean silently celebrated his victory.

Dean let the topic drop but thanks to Sam's ultra bitchy reaction he made a note for future pestering when the mood struck. 

* * *

 

Opportunity presented itself two days later when a somewhat injured Sam stubbed his toe on his way into the bathroom.  A nicer brother would have taken mercy, after all Sam did just bust his back badly on the last hunt, but Dean couldn't resist. "Jeez, Sammy.  Don’t take it out on the room. I can just punch you in the kidneys or something if you need to get it up to jerk off in the shower!" 

Sam responded by flipping Dean the bird and closing the door.  He made sure to take an extra long shower so all the hot, warm, and lukewarm water was gone when he was done.

* * *

 

Karma was a bitch for Dean about a week later.  He had a fairly nasty gash that was going to require stitches.  Sam wasn’t sure if claws or teeth caused it, but it got Dean on his right flank pretty good.  Sam had to drive back to the motel after jamming a towel against Dean’s side to put pressure on the wound.  Luckily for him, Sam had a steady hand and talent for stitching wounds. 

Unfortunately, they were completely out of painkillers and not in any position to be finding their friendly neighborhood pill peddler.  Dean took a long drag from his bottle of whiskey before starting, Sam didn’t let him have more than that.  "I don't need you bleeding out before I get you stitched up!" Stupid.  He was absolutely right, but it was stupid and really gonna hurt.  Sam was as gingerly as he could be while cleaning and disinfecting the area.  When he finally got to work Dean was biting down on his belt and gripping the sheets of the motel bed hard enough to leave little tears in the fabric. 

Sam was thorough and meticulous in stitching Dean up, like he was with everything else he did.  Great for the long run: it meant Dean wouldn't have some gnarly scar.  At the moment though, it hurt like a motherfucker and Dean was willing himself to pass out from the pain, even if it was only temporary. 

After what seemed like an eternity Sam laid a calm hand on Dean's bicep. "Almost done.  I just need you to sit up so I can bandage this." Dean rolled and Sam helped him sit up.  Sam grabbed the bottle of whiskey and the roll of gauze from the nightstand.  He handed Dean the bottle on his good side, "Arms up," and started wrapping Dean’s ribs where the fresh stitches and ointment was. 

Dean took a several chugs before pulling the bottle from his mouth, wincing, "Son of a - I honestly don't see how you pop a boner over how this feels.  This fucking sucks..." Dean trailed off taking another long pull from the bottle hoping that the alcohol would work quickly to take the edge off. 

Sam huffed in annoyance, "I don't _get off_ on being hurt, Dean..." 

"Sure you don't, princess - ow!" Sam gave an unnecessarily hard tug on the bandage. 

"I don't get turned on by getting hurt, idiot." Normally Sam would be angrier about it but he was concentrating on the task at hand. 

"So that constantly pushing on your bruised lip? What was that all about?" Dean started feeling the pleasant tingling in the tips of his fingers; meaning relief from a drunken buzz was probably on the way soon. 

Sam snatched the bottle from Dean and plopped down on the other bed. "I don't understand your fascination with this." It was Sam's turn to take a swig of liquor as he eyed Dean suspiciously. 

"'S just weird, that's all..." Dean swayed ever so slightly. "I mean we get banged up all the time... Why seek it out?" 

"It's not like that..." Sam took another swig.  Might as well catch up to Dean.   

"Look..." Sam leaned across the gap between the beds to hand Dean the bottle.  Dean had made his way to the head of the bed to sit up with pillows cushioning his injury.  He grabbed the bottle, took a swig, and handed it back across. Sam was unlacing his boots but grabbed the bottle, placing it on the nightstand between the beds.  "If you're talking about my reaction to when you _bit_ me while we were having sex with that girl... that took me off guard.  We've talked about this.  I was a little stunned - and don't even act like you didn't know what you were doing!" Dean shrugged.  "Maybe if we both weren't sex stupid at the time it wouldn't have happened, but I was in the middle of sex.  Obviously it felt good at the time.  I grabbed you impulsively, I admit it, but when you bit me it fucking hurt but made everything else feel more intense." 

"So I could have made you blow if I knew what I was doing and timed it right? Didn't know you were such a cheap date," Dean never could temper his commentary once whiskey started to have its desired effect. 

"It's not like that, it's just..." Sam raked his hands through his hair and took a deep breath to gather his thoughts.  "It only happened one other time.  With Jess.  We had been together maybe 7 or 8 months and had a strict policy that if I felt like I was close I would say something.  That way she'd get everything she needed without me cutting it short." 

"What the hell? If you bust a nut early, you just eat her out until you can get it up again.  Oral can be like intermission -" 

"Do you want to know what I was getting at or not?" Dean shut up and pathetically tried reaching for the bottle without moving too much.  Sam handed it to him and continued.  "Anyway.  One night we were going at it.  She was on top of me and I told her I was close.  She reaches back and slapped me, hard, right across the face. Then goes, 'Don't you dare!' I came from how intense it was.  I think I blacked out a little.  I'm not sure what happened.  It was definitely awesome though.  The next thing I vividly remember is her frantically apologizing and asking if I was ok... we talked about it afterwards.  I told her I really liked it and that it was enjoyable.  She hated it.  It scared the shit out of her.  She wasn't into the idea of hurting me, even if it was consensual, even if I was into it." 

Dean nodded. "So that's it?" 

"No," it was Sam's turn to keep drinking.  "In my free time, when Jess wasn't around, I would go on these porn sites and check out what the deal was.  I mean I knew there were other people who were into it, but I didn't know how far it went.  It was research, really..." 

"Riiiiiiight!" Dean wasn't gonna let that bullshit slide.  It might have been 'research' because Sam's intellectual curiosity got to him, but he could have read up on it.  Porn sites were not required.  "So did you convince her to get into it?" 

"No.  I mean don't get me wrong, sex with her was amazing, but it was mostly gentle and nothing too crazy." 

Dean scoffed, "So now every chick you bang gets the rough treatment to make up for it?" 

"Sort of.  I mean, I guess I never really thought about it..." 

Dean could see that introverted dialogue going on in Sam’s brain. "Hey! Don't do that. Everyone has kinks.  So did you ever get the chance to try out the kinky rough stuff with anyone? From your ‘research’." 

"Hell no! I would have done it with Jess because I knew her.  I trusted her.  You and I both know that I can't exactly  _volunteer_  to have some stranger give me the strange sex treatment.  Too many things could go wrong for a normal person - much less a hunter!" 

Dean started thinking, and maybe it was the pain or the alcohol talking, but he had to say it out loud, "What if you had backup going into it?" 

"What?" Sam was confused.  Maybe Dean was drunker than he looked.   

"What if you found one of those people and hooked up.  See if you're really into it.  And I'll be nearby so you don't have to worry about an ambush..." 

"Dean, you're drunk.  Let's drop this," admittedly, Sam perked up at the suggestion but would never ask his brother to go that far. 

"Why?" Dean wasn't switching into belligerent drunk mode, thank God.  He was just reduced to a three year old's capability to being told 'no.' "Not like we haven't fucked together.  Or watched... Ooooh that could be fucking awesome! I mean, I don't get off on the pain shit but seeing what some creative chick does to you -" he cut himself off with an exaggerated moan.  Suddenly, the air was too thin and Sam's jeans were definitely too tight.  Fuck him.  Fuck Dean and his fucking fuckery! Sam would be damned if he thought that there was anyone who could mess with his head better than Dean.

* * *

 

Dean was a superstar at research when he was on a mission.  He was not too drunk to remember that conversation the next morning.  Luckily for him, Sam was a great brother and acquired stronger painkillers by lunchtime the next day.  That meant that Dean was left to be in a drug-induced relaxation with nothing but free time on his hands for a day or two.  Sam went to the library to research and Dean had Sam’s laptop in the room. He started researching how people into what Sam was talking about and after falling down that rabbit hole he decided he’d need to have an uncompromised mental state to process a lot of the intricacies of this lifestyle and what’s acceptable for a person just trying it out. 

Several weeks went by until Dean had the proper amount of free time to dedicate to this without Sam immediately in the area.  Careful research bought Dean to one final conclusion, and it meant breaking a long-standing policy of his own.  It was just safer to pay someone to do it.  Yep, it violated his ‘No Cash For Ass’ policy but Sam’s safety took precedence over that.  Not surprisingly, Dean found most major cities had at least a few people who were doing this job professionally.  Also not surprisingly, more white-collar business people in the city meant more of these BDSM for hire professionals.  

Once Dean came to this conclusion, he waited until Sam was trapped in the car on the highway to broach the subject.  It was awkward, to say the least.  After some very frank and uneasy discussion Sam agreed to let Dean work on the arrangements for this as long as a hunt wasn’t taking priority.  As long as the person or business agreed to let Dean stay while Sam was in the session, they would move forward with this.

* * *

 

Manhattan. Dean hated Manhattan. Out of all the places in the world, he did not willingly go in there.  Too many unaccounted for factors and innocent bystanders, then add the fact that New Yorkers are fucking crazy to the mix.  He knows of hunters who spend their time clearing shit out in just the five boroughs fulltime for years without making a dent. Fate had it that he was looking for a professional business to do this thing for Sam, and they happened to have a case that wrapped up in the Pinelands of New Jersey.  And if the online reviews were to be believed: if you’re going to do it you do it here.  

After a few email exchanges the brothers ended up at this “dungeon” for an interview with one of the women running the place.  She was a middle-aged woman, maybe late 40s, and wore a tight fitting but otherwise professional suit with a high cut blouse under her jacket. Clearly, she was dressed for the business end of this.  She handed Sam paperwork, a checklist, where he’d check his likes and dislikes. She said it was to help them narrow down the most appropriate match for what he was looking for. Dean was astounded at how long the list was, but after seeing so many people the place probably had time to perfect it. 

She took the opportunity to chat with Dean.  She wanted to gauge how serious he was about just watching.  The place didn’t have a problem having two clients in the room, they’d be paying for two regardless, “I just need to know if I should be sending two people in or one.” She said it with a wicked grin that reassured Dean, in some bizarre way.  

Once she had a chance to discuss with both of them and check the schedule, she gave them a price and told them to come back at 7:15pm for the session.  They killed the rest of the morning and the entire afternoon easily enough.  Manhattan may be insane, but there was certainly more than enough to do to fill a day. By dinner, Sam was visibly nervous.  Dean did his best to not push Sam one way or the other, but he’d definitely be bummed if Sam decided to call it off at the last minute.

* * *

After some quick introductions and exchanges about safewords and warnings, “Tatiana” brought them to the room where this would all go down.  She explained the ground rules of the scene: Sam wasn’t allowed to speak unless it was to pause or stop.  Dean would speak for Sam; although Dean wasn’t planning on actively participating he wouldn’t object to that rule.  They had an hour but could reserve the right to extend time since her next client had to reschedule.  After laying out a general idea of what was in store, the brothers had an opportunity to ask questions.  That’s when it got underway… 

Tatiana told Dean to make himself comfortable in the plush armchair.  Then instructed Sam to strip down to his underwear and kneel on the padded place in the middle of the floor.  This was the first opportunity Dean had to get a good look at the woman.  She wore black vinyl, like he assumed she would, in the form of a military style jacket with slits on the slides and back, a matching g-string, thigh high stockings, and six-inch stilettos.  She completed her look with blonde hair slicked back in a bun, dark heavy eyeliner, and red lips – she certainly looked the part.  She retrieved a pair of padded leather cuffs from a table along the wall and walked over to Sam.  Sam was extremely eager to comply, already stripped and kneeling, but his nerves had him fidgeting.  She took one wrist and secured the cuff with a pair of buckles, “Too tight?” Sam shook his head no.  She repeated this with his other wrist then brought both behind his back.  The cuffs had hooks that interlinked; Dean noted that they looked like quick release in the event of an emergency. She left his arms bound behind him and walked back to the table.  Sam was facing with his back towards Dean, so Dean was switching from watching the dominatrix and watching Sam’s back muscles twitch with anticipation. She had picked up a riding crop from the table and walked back to the bound Sam.  

The riding crop touched lightly in the center of Sam’s chest and slid slowly up his chest and neck, she pushed harder into his neck and pulled up.  She forced Sam’s chin up until he was looking up at her. She didn’t move the riding crop when she looked over at Dean and spoke, “Your brother brought you here because you were misbehaving.  Dean says you need discipline.  Tell me, Dean, how was Sam disciplined as a child?” Sam shivered with anticipation. This was completely humiliating but making his hard as nails.  

Dean shifted in the chair and cleared his throat. “Our dad would, um, spank us.  If we were really bad, we’d get the belt. We would have to do extra chores most of the time.” 

“Hmmmm,” she looked back at Sam, “That’s not working enough now, is it?” She starts walking around him so that she can access his back.  Starting at the elastic of his boxers, she starts lightly dragging the riding crop up the center of his spine agonizingly slow. “Have you been a bad boy?” Sam couldn’t help the full body shudder at the question.  

“Yes,” Sam responds. 

He gets a hard crack across his back as a punishment, “Did I say you could speak?” Sam involuntarily moans, which was perfectly allowed, and arches into the dead air in front of him. Dean leans back in his chair and unconsciously puts his palm to his crotch to relieve the pressure.  Maybe Sam was onto something with this. 

“You can take off whatever you’d like to get more comfortable, Dean,” she looked at Dean and held eye contact. “Do you think perhaps you just need a studied hand to show you how to properly spank him?” Dean gave an aroused groaned in response and that’s all she needed to continue. “Would it be more helpful to see his face or his ass while I instruct you?” Sam moaned and dropped his eyes, she responded immediately, “Eyes up! I didn’t tell you otherwise!” Sam felt a blurt of precome start to soak through his boxers at that command; he moaned in response but obeyed and flicked his eyes back up.  

Dean didn’t know whether it was his own kink about having a woman boss him around or his gripe that Sam was always so difficult, either way, he was scrambling for his belt and fly to relieve the pressure on his dick.  Tatiana spoke up again, “Sorry for the interruption. Which position would you prefer him in?” She raised an eyebrow and waited for the response. 

Dean tugged his jeans down to the middle of his thighs but left his boxers intact, for now. He met her glaze and finally responded after a few seconds of thought, “Wanna see his ass.  Show me how to properly discipline this mouthy fucker.” 

She moaned in response, no way to tell if it was genuine or not.  “Stand up!” She smacked the middle of Sam’s back with the crop for emphasis. She gestured to the leather-covered contraption that looked almost like a gymnastics vault to Dean.   It was only a few feet from the chair Dean was sitting in. “Go over there and lean over it.” 

Sam struggled a little bit but was perfectly capable of going from kneeling to standing without use of his hands.  He draped himself over the bolstered piece of furniture like he was told.  He eagerly waited for what was next, for Dean’s sake he checked that he was okay with everything up to drawing blood. He knew Dean would pull the brakes if he saw blood, although a deep down part of Sam wanted to be battered, broken, and bleeding at the end of this.  Sam got an eyeful of what other restraints were available to be used on him from this particular piece of furniture and moaned to himself. There seemed to be a wide assortment of methods for this, he would be surprised every time she moved him. This was either going to be great or cut embarrassingly short. 

She walked back over to the table and picked up two items: a paddle and a leather-tassled item with a handle.  Dean had seen them in porn before but didn’t know what the hell the proper name for either was. “Do you have a preference? I feel like maybe you just need to our Sam a proper motivation to behave himself.” 

Dean gestured to her left hand, “Paddle.” 

She smiled and placed the other object down.  “You could get more comfortable Dean.  I’m sure it’s a little warm in here for you.” Dean got the hint; she smiled as he shed his unnecessary layers and stripped down to his dark t-shirt but made no additional efforts to undress.  She approached Sam and put a hand firmly on his back, she almost gently ran down the backs of his arms to the cuffs, unhooking them and pushing his arms forward.  Sam got where she was going and moved so his arms were dangling forward over the bolster. She moved so she was in front of him.  With his eyes up, face forward position, Sam’s face was just a few agonizing inches from her crotch.  His reaction didn’t go unnoticed, “You want some pussy?” 

Sam nodded enthusiastically.  A quick, “Yes,” rang out from Dean.  The room wasn’t that large so her speaking to Sam in anything above a whisper would be heard by both men.  

“You are being punished for bad behavior, Sam.  Maybe if you learn to be a good boy.  Good boys get pussy, right Dean?” 

“Right,” Dean was fast to respond. Now he was actively pushing the heel of his hand into his boxers to try to keep his erection at bay. This started out being about Sam but this was giving Dean a look at kinks he didn’t even know he had. 

“You are a good boy, right Dean?” 

“Yes, ma’am.” 

“Ma’am? See Sam, he has such good manners.” She knelt down to pick up a chain from the underside of the furniture and started to secure Sam’s wrists to it.  “I think you want to be a good boy. You just need the proper motivation.” She yanked Sam’s boxers down to the middle of his thighs and walked over to Dean, laced her fingers in his hair and jerked his head back. Dean let out a whimper in response, he didn’t think he was going to be an active participant in the proceedings but certainly wasn’t going to argue now.  She moved so that one of her legs was between Dean’s and the other was on the arm of the chair Dean sat in.  She pulled his head closer to her crotch as she continued to speak, “Why don’t you show us how good boys behave?” Dean didn’t miss a beat. He immediately kissed her inner thighs and licked along the line of her vinyl g-string, only a little weirded out by the smooth texture on his tongue.  He slid his hands up to the sides and was pleasantly surprised that the garment was tied on; he flicked his tongue over the vinyl to rub her clit as he pulled the ties loose.  She let out a genuine moan that time.  He was able to pull the underwear away while he kissed her thighs again, and then moved back over her pussy.  He approached it just as he would her mouth, placing several short, firm kisses over her vulva before being more insistent and sliding his tongue over it. He was kneading his fingers into her butt cheeks as he did this.  He dipped his tongue into her then moved in a smooth stripe over to her clit, he flicked his tongue a few times because sucking the swelling nub, slowly rolling his tongue over it while maintaining suction.   

Sam could hear the moaning and tried, in vain, to crane his neck to look.  His position made it impossible.  He couldn’t shift his weight to look because the secured position made it so he was more on his toes.  The chair’s placement was directly behind him, so he couldn’t even partially see what was going on.  He let out a whine.  “Only good boys get to watch, Sam,” she sounded breathy.  It might not have been intentional; she probably wasn’t expecting the Dean Winchester Cunnilingus Treatment when she walked over there.  

Dean started rubbing his hands up her stocking-clad legs as he continued his alternation between sucking and licking.  Abruptly, she jerked his head back.  He was forced to look her in the eye as she spoke, “You are very good at this. Most good boys are, but you are a _very_ good boy.” Dean blushed and tried to drop his gaze.  He is terrible at taking compliments.  “Eyes up!” He blushed even more profusely because he wanted to obey, further proving the point that she was trying to make.  “But you are here to teach Sam to be a good boy too, right?” 

“Right.” 

“Tell me what some of Sam’s bad behavior has been lately,” she almost coos as she runs her hand down the side of Dean’s face.  It’s an intentional contrast to the way she’s treating Sam.  “I need to know so I can determine the appropriate punishment.” 

Dean tried to think, but he must look pale because all the blood in his body rushed south to his now very interested erection.  She’s overwhelming to Dean; Sam is torn because they are talking about him like he isn’t a few feet away.  Whatever the cause, all of these conflicting and frustrating emotions are actually turning Sam on even more.  Dean cleared his throat, “He always forgets to get pie for me when he goes on a food run, even though I specifically request it every time.” 

Sam couldn’t stop himself, “Are you fucking serious? I told you I wasn’t getting it because you need to eat healthier!” 

Tatiana acted swiftly, picking up the paddle and landing an authoritative strike across the middle of Sam’s cheeks.  Dean was a little stunned; he was fascinated watching the flesh grow an angry dark pink shade in the paddle’s wake.  Sam was stunned but it was the first firm physical contact he had in the session. He let out a high pitched keen as he rocked his erection against the bolster. “Disrespectful and bad. You really do need to be disciplined, Sam.” She shifted her gaze back to Dean, “Is he always like this? Foul mouthed and full of back talk?” 

Dean was enthralled. It’s like she was a vampire or something, the way she was sucking him in.  He knew she wasn’t because he subtly tested for that before the session started.  Not that he even cared at this point, “Yeah, er, yes.  He likes to complain a lot too.  Always complaining about my driving music and my singing, even though there’s a car rule about driver picking the music.” Sam shifted this time but kept his mouth shut. “And whenever he drives my car, he brings her back dirty.  Doesn’t show her the proper love and affection.” Oh, how he’s just goading Sam into breaking a rule again. “And he doesn’t like how I tell him to be more gentle with women in bed. He doesn’t understand the benefits of being sensual.” 

Tatiana grabbed Sam’s hair to jerk him up slightly and whispered hot against his ear, “I don’t understand the benefits of being gentle either.” Sam moaned, loudly, from that. He was allowed to moan as much as he wanted to, just not speak.  She let him go and looked back to Dean.  Dean couldn’t hear what she said to him, but Sam’s moan had Dean pushing against his hard on again.  Tatiana gave him a command for the first time, “You’re overdressed, Dean. Good boys strip if they want to learn from me.” Dean practically scrambled out of his clothes. He unlaced his boots just enough to kick them off, then yanked off his jeans, boxers, and socks before discarding his shirt and sitting back down.  “So eager to please.  You even remembered to sit back down without being told.  I like your matching tattoos.” Dean was blushing again. “Sounds to me like Sam’s bad behavior calls for… fifteen strikes.  Does that sound fair to you?” 

There wasn’t enough oxygen in the room.  That’s what Dean concluded the problem was.  “Yes, ma’am.” 

She let out an exaggerated moan, “Such a good boy.  Are you always so pretty and eager?” It was a rhetorical question but had the blush spread to Dean’s chest.  “Because you’re a good boy, you are going to count them for me.” Dean nodded, he wasn’t sure how well his voice would work but he would do it. She stepped over to the left of Sam and landed a firm strike just where his leg meets his ass, just where it’ll sting the most.  

“One,” Dean quickly got it out. 

“That’s ‘One, thank you ma’am,’ to you.  Don’t forget your manners,” she wasn’t going to let Dean get comfortable in this scene. 

“One, thank you ma’am!” Dean was enthusiastic. 

“Good boy.” She tapped the paddle over Sam’s skin before ratcheting back and landed a hard blow just above the previous one. 

“Two, thank you ma’am.”

“See Dean, I think Sam’s learning not to be a bad boy already.  It does seem to be motivating him…” She trailed off and ran a hand down his cheek to cup his balls.  Sam’s cock was leaving a wet puddle of precome on the floor from how much he was leaking.  He wasn’t kidding about being really turned on by this.  She started rolling his balls in her hand and Sam let a small “Please…” escape his lips.  She swatted his balls with two quick slaps, “No talking.  That includes begging, bad boy.” She turned slightly to Dean, “The only begging that’s going to happen is if Dean begs for you.” Dean wasn’t sure when he started pumping his own cock at the scene unfolding in front of him but his pace quickened. 

She pulled back and landed four quick, softer hits in a row.  “Three, four, five, six, thank you ma’am!” Then one harder blow on each cheek, “Seven, eight, thank you ma’am!” Dean cut off into a loud moan. Sam was squirming from the contact, trying to get pressure and relief for his cock.  The angle couldn’t really let him hump the furniture, just brush against it.  She landed three more fast hits, alternating cheeks.  Sam let out a loud grunt on each one.  “Nine, ten, eleven, thank you ma’am.” 

She ran a hand over the angry raise welts to contrast the blows, her hand felt cold to him against the hot skin.  Sam made some unintelligible noise as she did that.  She looked at the clock on the wall then spoke to Dean, “Almost there.  Do you think this is improving his attitude?” Dean nodded with an exaggerated swooping up and down, moaning instead of responding.  

She resumed, landing the final blows lower where she originally started.  “Twelve, thank you ma’am.” Another harder than the previous. “Thirteen, thank you ma’am.” Harder. “Fourteen, thank you ma’am.” She put full force behind her final blow, direct hit on the center of Sam’s ass. “Fifteen, thank you ma’am.” Sam was panting hard, shaking from how hard he was.  He should have requested a cock ring or something. 

Tatiana walked around to the front Sam and he looked up to meet her gaze.  His pupils were blown wide and she could tell he let a tear or two loose during the spanking.  She ran a thumb down the tear trail on his one cheek, “So beautiful.  Maybe you have the makings of a good boy after all.” She tugged his hair just to get a whimper from him. She held his eye contact, “There are rewards for taking your punishment properly.  Just because you’re a bad boy, doesn’t mean you don’t get to come…” Sam and Dean both moaned at that.  “Would you like that?” 

“YES!” Dean was beyond caring how he looked in this situation. 

She leaned in to whisper where only Sam could hear her. “I think we can make that happen, don’t you?” Sam nodded quickly against her, not that she needed to see his response. “I think your ass deserved a reward.  Do I need to prep you or are you good to take something without? Speak!” 

“Without!” Sam was quick to respond.  It actually made Dean jump because he hadn’t heard the instruction for Sam to speak. 

“Hmm, I like your ambition, bad boy.” She walked over to the table again and put on a pair of latex gloves.  Dean readjusted how he was sitting to see what she was doing.  She picked up a large tube of lube and a toy from the table. Dean groaned and leaned back in the chair, though he slowed his jerking off to a lazy pace. He had a feeling it would be worth holding out. 

Dean recognized the toy when she got closer with it and deliberately made a show of lubing it for Dean’s benefit.  He knew from some particularly adventurous hookups that it was some sort of prostate stimulator. It was black and curved like a wobbly letter C.  It looked like it had two more bulbous areas on the part that would be inserted, so it was different than the ones than had been used on him.  He groaned as she lubed it in slow strokes.  Although Sam said he could take it without prep, she slid a lube-coated finger over his hole.  Then she snapped the elastic of the boxers, still around his thighs, against his legs.  He yelped from the sudden snap and cut off into a moan as she slid a generously lubed finger into him.  She pressed then withdrew and pressed again inside him, he let a loud keen out that time. “That’s what I thought,” she said more to herself as she withdrew her hand.  

Then she was pressing the toy to into him, just the right side of too much for Sam. He liked feeling stretched open by it and feeling a slight burn.  She slid it in and out a few times before fully seating it in him. She hit the switch to turn the vibration function on and held it in place.  Sam practically howled as his eyes went wide and arched his back, even in this position.  His hips tried to fuck the air.  The toy was designed to vibrate towards his prostate from two angles, one from his perineum and the other from inside him.  She turned up the vibration by two settings and pressed it hard to his taint.  She ran her other gloved hand over his balls and Sam was practically sobbing.  His panting and broken high-pitched moans filled the room.  He was close; Dean could tell he was close.  Dean was matching pace, dangerously close to the edge himself.  

That was when she removed her hand and yanked the toy from Sam’s body abruptly.  Sam was close, really close and then all stimulation was gone.  He screamed in frustration and thrashed against his restraints.  He couldn’t contain his outburst, “SON OF A BITCH! NO! No – please it’s not fucking fair you said I could come!” 

She stopped listening and let him bitch to the wall about how upset he was.  She knew she’d get a reaction like this from him. While he ran out of steam she turned to Dean with a smug smile.  Dean was at a loss as to what to do.  He hadn’t come when Sam was close and now he knew Sam broke all kinds of ground rules with that outburst.  “What a good boy.  You even wait to come with your brother.  A good boy and a gentleman.” She ran her free hand over his chest.  “You’ve been so good, you deserve a reward. In fact, you’re so good I might even let you _pick_ your reward.” She leaned in to whisper in his ear, Sam still cursing up a blue streak in the background.  “What would my good boy like for a reward?” 

Dean didn’t even hesitate, “Wanna make you come.” He certainly was not a typical client, but not an entirely uncommon request in this line of work.  

She pushed him back in the chair and looked over at the clock again.  She threw a foot on the arm of the chair again, the other on the floor, and braced her hands on the back of the chair.  “You have four minutes to try to make me come, good boy.” That was all Dean needed to lunge up and go back at her clit and plunge two fingers into her.  She decided to play on his need for approval.  “So talented at this.  Did you go to pussy licking school or were you just born this talented?” Dean moaned into her and the reverberations from it felt fantastic.  Admittedly, she was already soaking wet from this session.  Dean had her warmed up earlier, but she was enjoying how hot both men were since she was told about them earlier in the day.  Not that all the clients there are schlubs, but these two were exceptionally good looking.  The fact that they played into what she had planned for the session just made it more delicious. Dean crooked his fingers inside her and re-upped his efforts.  She started to moan loudly as the squelching sound of his fingers working overtime started to ring out.  “I’m close, good boy,” she panted out and gripped his hair.  “Want me to come on your face? Give you a squirt bukkake?” Dean moaned loudly and leaned back.  His lust blown eyes said the entire ‘Yes’ that she needed to hear. She pushed him back onto the chair and started firm, rapid strokes with her fingers over her clit. She was practically straddling Dean.  

“Please, give it to me, please,” Dean managed to pant out as he was rubbing her thighs in encouragement.  Little more hard flicks and she was coming, gushing onto Dean’s face as promised. She kept up her motions to ride through it, ensuring Dean got all of it.  When she stood up, Dean whispered out, “Thank you.” How he had managed to keep from coming was a mystery to her, but she was impressed with his stamina. 

She still had the toy in hand and walked back over to Sam.  She went to look at him face to face.  “Even though you had that rude outburst, I’m still going to let you come.  I’m going to put you in a different position though, are you okay to move?” Sam nodded. “Good.” She unclipped the cuffs where they were secured and moved to help him stand.  She brought his arms behind his back and clipped them behind his back again.  She grabbed a large pillow from the unused couch on the other side of the room and threw it on the floor close to Dean.  “Lay down, flat on your back facing me.” 

Sam complied. He sat on the floor and adjusted his shoulders and hands so that he could lie back comfortably. He had his hands at the small of his back and leaned back onto the pillow with his knees bent, feet on the floor, head practically at Dean’s feet.  She brought a pad with her and knelt on the floor between Sam’s legs.  “Here’s how this is going to work,” she put a hand on his knee.  “I’m going to put this in you again, and we’re going to start where we left off.  You can come whenever you want, but no talking.” She hooked her arms under his knees and rolled him up so his knees were almost touching his chest. He was taking most of his own weight on his shoulders. She reapplied lube to the toy and pushed it back into him.  When she turned the vibration back on, Sam couldn’t even make a noise.  His mouth dropped open and his head thudded back onto the pillow as his eyes rolled back.  She turned it up one more notch; he let out an unnatural high noise and shook. 

Dean was pumping his cock furiously. “Come on, Sammy. You’ve got this,” he panted out. He was so close but he didn’t want to come first this time.  Sam let out another strangled noise as she turned up the vibration and pushed it hard against him.  “He needs help, ma’am.  He needs a hand on his cock.” 

Tatiana totted him, “I think he’s going to come just like this.  Good boys come just from something in their ass. Go on, show me you are a good boy.” That was it.  Sam started to come and the angle this dominatrix had handled him into made it so he was going to make himself sloppy in the process.  The first spurt hit him in chin and upper part of his chest. That was when Tatiana finally put a hand on him, jerking him through it and purposely angling his cock so he’d come on his own face.  Dean was close behind him, making that tell tale noise that said he was seconds away from blowing his load.  Tatiana spoke up then, “You.  Come on him too.” Neither of them was with it enough to object, and it made sense in the moment. Dean got out of the chair and knelt by Sam, it only took six quick strokes to start coming, most hitting Sam’s chest right over his tattoo.  

Dean braced his free arm on the chair to steady himself through the initial aftershocks. Tatiana carefully removed the toy and placed Sam’s legs back on the ground.  She rolled him slightly to release the hooks on his cuffs and pulled him arms out from underneath him.  Even though Sam was basically dead weight right now, she seemed like she had plenty of practice at it.  She got up and walked over to the table to deposit the toy and back on it and removed her gloves.  She grabbed a bottle of lotion and two bottles of water.  

She approached Dean first, handing him a bottle of water, “Drink up.  Trust me, you need to rehydrate.” Dean was a little shaky as he took a sip.  He was definitely going to need a few minutes.  Meanwhile Sam looked completely checked out.  They did get a warning that it could happen when they initially got into this.  Hell, it was consistent with his story from when he’d done something way tamer than this. 

She approached Sam next, sitting down on the floor next to him.  “Hey Sam, you in there? I need a nod at least.” Sam was fuzzy but did nod.  “Do you want me to clean you up? You don’t look like you’re in any condition to be doing it yourself.” Sam nodded.  She got up off the floor and went to a cabinet in the corner, retrieving a towel and some baby wipes.  She worked efficiently, wiping most of the semen off Sam with the towel, and then going back over the area with a baby wipe.  He was grateful because he didn’t want to be walking around with drying come on him.  She looked over at Dean, who appeared to have mostly recovered by now, “Feel free to get dressed, I just need to make sure he’s got the proper care and watering after the scene.” She tapped Sam on the shoulder, “I need you to roll over.” He complied and she inspected the welts from the earlier paddling, they were raised but no broken skin.  She ran a hand over one cheek, “Do you want lotion on this?” 

Sam finally attempted speech, “No.” He sounded like he’d been gargling with razorblades but could speak at least.  Dean raised an eyebrow but said nothing.  It wasn’t his place to lecture right now.  Dean had gotten to the point of getting his boxers, jeans, and t-shirt on and sat down to put his socks and boots on.  She removed the cuffs from his wrists then placed a hand at the small of Sam’s back.  “Need anything from me?”  Sam shook his head to indicate ‘no.’ She looked over at Dean, “How about you? Do you need anything?” 

Dean thought about it. He gave her a genuine smile, “No, I’m all good.  Thank you.” 

She stood up and walked over to Dean.  He stood so they were face-to-face.  “Well, you have ten minutes to decompress and get dressed if you need it. Hit the light switch next to the door if you need help getting him up and out the door.  That happens sometimes.  It was great meeting you.” 

Dean dug in his jeans pocket and pulled out a wad of cash.  He handed it to her, “Thank you very much.” He flicked his gaze over to Sam, who had stirred enough to get his jeans and underwear on and was working on his socks.  “You need help over there?” Sam gave a groggy thumbs up. 

Tatiana turned to him, “Great to meet you too, Sam.  Hope to see you back again.  We have only just scratched the surface.” Sam smiled back to her and with that she made her exit. 

* * *

 

Sam was able to get dressed on his own and with Dean’s help got out of the place without incident. Sam was a little wobbly on his feet to start with but they were able to make it back to the car. 

Dean broke the silence after thirty minutes on the road, “So is that what you were looking for?” 

Sam burst out laughing.  He was so far into his own headspace he wasn’t expecting Dean to ask some equivalent of ‘how was it for you?’ He took a deep breath and turned to Dean, “Way better than what I thought it’d be!” 

Dean lit up, flashing a smile that he only reserves for ‘Sam is happy so I’m ecstatic’ moments, “Great! Because that was awesome! I might need a few days to process how fucking awesome it was.” 

Sam couldn’t resist, Dean left the door open, “So maybe you are seeing the benefits of rough sex after all.” 

That fucker. This is why they can’t have nice things.  “No! I still don’t think it’s all you make it out to be, but it has its merits. Talk to me tomorrow when you have to sit on your bruised ass for twelve hours while we drive to Georgia.” 

Sam cringed just a little.  That might actually suck, a lot.  “Pretty sure I’m not going to change my mind on how much I enjoyed it though.  Definitely going to have to do that again.” 

Dean raised an eyebrow, “Yeah?” 

Sam smiled back at him, “Yeah.”

**Author's Note:**

> Kudos make me smile and comments make me giddy. If you have a scenario that you'd like to see these two in, I'm certainly open to ideas. I can't draw all my inspiration from porn :)
> 
> Partially inspired by this gif on Tumblr  
> http://straponfemdomgif.tumblr.com/post/122444705527  
> Go over to Tumblr and give it a heart if you like it too  
> 


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